DIOSMETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O6
Molecular Weight	300.2629
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1O)C2=CC(=O)C3=C(O2)C=C(O)C=C3O

InChI

InChIKey=MBNGWHIJMBWFHU-UHFFFAOYSA-N

InChI=1S/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H12O6
Molecular Weight	300.2629
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27725131 | https://www.ncbi.nlm.nih.gov/pubmed/28835383 | https://www.ncbi.nlm.nih.gov/pubmed/24092244

Diosmetin is the aglycone of the flavonoid glycoside diosmin, which occurs naturally in citrus fruits. Diosmetin is found in the legume Acacia farnesiana Wild and Olea europaea L. leaves. Diosmin is hydrolyzed to its aglycone diosmetin by intestinal microflora enzymes before its absorption into the body. Pharmacologically, diosmetin is reported to exhibit anticancer, antimicrobial, antioxidant, oestrogenic and anti-inflammatory activities. Diosmetin increased inhibitory GSK-3beta phosphorylation, while selectively reducing gamma-secretase activity, Abetta generation, tau hyperphosphorylation and pro-inflammatory activation of microglia in vitro, without altering Notch processing. Therefore, diosmetin could be considered as potential candidate for novel anti- Alzheimer's disease therapy. Diosmetin is ER-beta agonist and potential novel drug for the acute myeloid leukemia treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A1 32 Target ID: CHEMBL2231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	140.0 nM [IC50]
Cytochrome P450 1A2 73 Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	2.4 µM [IC50]
Cytochrome P450 1B1 4 Target ID: CHEMBL4878 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20696580	Inhibitor 8504	29.0 nM [IC50]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383	Agonist 2752
NF-kappa B signaling pathway 87 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 141 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28835383	Primary	Preclinical	Unknown Approved Use Unknown
Hepatocellular carcinoma 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28101238	Preventing	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27725131	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.	2015-03	25388478
Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids.	2011-05-01	21482471
Beta-glucuronidase from Helix pomatia origin is not suitable for diosmetin analysis.	2010-12-01	20656432
Effects of plant-derived polyphenols on TNF-alpha and nitric oxide production induced by advanced glycation endproducts.	2010-07	20540146
Why do we need multifunctional neuroprotective and neurorestorative drugs for Parkinson's and Alzheimer's diseases as disease modifying agents.	2010-06	22110336
Flavonoids and antioxidant activity of Rosa agrestis leaves.	2010-04	20397108
Simultaneous determination of diosmin and diosmetin in human plasma by ion trap liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: Application to a clinical pharmacokinetic study.	2010-03-11	19800189
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.	2010-03-02	20479987
Effects of Various Flavonoids on the α-Synuclein Fibrillation Process.	2010-01-28	20976092
Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro.	2010	20877134
[Chemical constituents of Galium verum].	2009-11	20209910
[Studies on flavones from Flos Chrysanthemi Indici].	2009-10	20112712
Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells.	2009-09	20183323
[Chemical constituents of Lobelia chinensis].	2009-09	19943485
Antioxidant Activity of Caffeic Acid through a Novel Mechanism under UVA Irradiation.	2009-07	19590707
Cytochrome P450 CYP1A1: wider roles in cancer progression and prevention.	2009-06-16	19531241
Anticancer effects of the flavonoid diosmetin on cell cycle progression and proliferation of MDA-MB 468 breast cancer cells due to CYP1 activation.	2009-06	19424633
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.	2009-03-25	18835421
Trihydroxynaphthalene reductase of Curvularia lunata--a target for flavonoid action?	2009-03-16	19010313
The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece-Crete indicates a new commercial source of hesperidin.	2009-03	18823075
Bioactivation of the phytoestrogen diosmetin by CYP1 cytochromes P450.	2009-02-08	18976853
[Studies on chemical components of Lobelia chinensis].	2009-02	19445152
Ecdysteroids and a sucrose phenylpropanoid ester from Froelichia floridana.	2009-02	19254799
Acasiane A and B and farnesirane A and B, diterpene derivatives from the roots of Acacia farnesiana.	2009-02	19101886
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009-02	19014974
Simultaneous determination of the flavonoid aglycones diosmetin and hesperetin in human plasma and urine by a validated GC/MS method: in vivo metabolic reduction of diosmetin to hesperetin.	2009-02	18850579
Iron behaving badly: inappropriate iron chelation as a major contributor to the aetiology of vascular and other progressive inflammatory and degenerative diseases.	2009-01-08	19133145
Stimulatory constituents of Eclipta prostrata on mouse osteoblast differentiation.	2009-01	18683850
Oregano: a source for peroxisome proliferator-activated receptor gamma antagonists.	2008-12-24	19053389
A new ferulic acid ester and other constituents from Dracocephalum peregrinum.	2008-10	18958424
Effect of flavonoids on rat splenocytes, a structure-activity relationship study.	2008-08-15	18590707
Flavonoids from Galium verum L.	2008-07-19	18636371
Camptothecinoids from the seeds of Taiwanese Nothapodytes foetida.	2008-06-16	18596662
New features on the fragmentation and differentiation of C-glycosidic flavone isomers by positive electrospray ionization and triple quadrupole mass spectrometry.	2008-06	18470889
Diosmetin induces human osteoblastic differentiation through the protein kinase C/p38 and extracellular signal-regulated kinase 1/2 pathway.	2008-06	18269307
Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.	2008-04-01	18249545
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in murine microglia and macrophages.	2008-04	18186104
Flavonoids diosmetin and luteolin inhibit midazolam metabolism by human liver microsomes and recombinant CYP 3A4 and CYP3A5 enzymes.	2008-03-15	18191104
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].	2008-03	18536375
Different flavonoids present in the micronized purified flavonoid fraction (Daflon 500 mg) contribute to its anti-hyperpermeability effect in the hamster cheek pouch microcirculation.	2008-02	18277344
Two new flavonoids from Origanum vulgare.	2008	19023817
Complete assignments of NMR data of 13 hydroxymethoxyflavones.	2007-12	17987643
A new flavone glycoside from the fruits of Luffa cylindrica.	2007-12	17689887
Raddeanalin, a new flavonoid glycoside from the leaves of Salix raddeana Laksh.	2007-08-19	17701556
Pensteminoside, an unusual catalpol-type iridoid from Penstemon gentianoides HBK (Plantaginaceae).	2007-07	17507063
Anti-proliferative and antioxidant constituents from Tecoma stans.	2007-02-14	17294687
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.	2007-02	17108059
Inhibition of pro-inflammatory markers in primary bone marrow-derived mouse macrophages by naturally occurring flavonoids: analysis of the structure-activity relationship.	2006-10-16	16934226
The efflux of flavonoids morin, isorhamnetin-3-O-rutinoside and diosmetin-7-O-beta-D-xylopyranosyl-(1-6) -beta-D-glucopyranoside in the human intestinal cell line caco-2.	2006-08	16832612
Polar constituents from the aerial parts of Origanum vulgare L. Ssp. hirtum growing wild in Greece.	2006-07-26	16848522

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50mg /kg/every other day for 6 weeks

Route of Administration: Intraperitoneal

In Vitro Use Guide

Diosmetin caused G1 arrest at 10 microM in MDA-MB 468 cells after 48-h treatment whereas this effect was not observed in MCF-10A cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:48:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:14 GMT 2025`
Record UNII	TWZ37241OT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4'-METHYLLUTEOLIN

Preferred Name

English

DIOSMETIN

Official Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-

Systematic Name

English

3',5,7-TRIHYDROXY-4'-METHOXYFLAVONE

Systematic Name

English

DIOSMETIN [MI]

Common Name

English

5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

DIOSMETINE

Common Name

English

LUTEOLIN-4'-METHYL ETHER

Common Name

English

CYANIDENON-4'-METHYL ETHER 1479

Common Name

English

DIOSMETOL

Common Name

English

Diosmetin [WHO-DD]

Common Name

English

5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

FLAVONE, 3',5,7-TRIHYDROXY-4'-METHOXY-

Systematic Name

English

Classification Tree Code System Code

DSLD

4156 (Number of products:7)